Potassium-zinc induced synergic enhancement of the basicity of hexamethyldisilazide (HMDS) towards methylbenzene molecules

Chem Commun (Camb). 2003 Feb 7;(3):406-7. doi: 10.1039/b211392a.


While neither KHMDS nor Zn(HMDS)2 can unilaterally metallate toluene under the conditions studied, the bilateral base 'KZn(HMDS)3' can smoothly do so to produce the benzyl product [[KZn(HMDS)2(CH2Ph)]infinity], which exists in the crystal as an infinite spiral chain of benzyl (ambi-sigma, pi)-linked (KNZnN) rings.